The media team and intelligence handlers around Edward Snowden finally committed a major blunder. After fawning tributes, softball interviews, and an Oscar coronation for his celluloid enablers, they made a decision they should have known would go wrong.

They let Ed talk to John Oliver.

This is nothing short of amazing, and suggests either that the Russian spooks now in control of Snowden’s life don’t watch Oliver’s show, or that they were led to believe Oliver is just another liberal journalist who would allow Snowden to run his usual All-American Kid act. Either way, they had to be disappointed. Oliver, for all of his attempts to be serious, couldn’t help but shove Snowden around, and the interview showed just how uncomfortable someone like Snowden is—and likely has been his whole life—around Cool Kids like John Oliver.

So, Snowden’s socially awkward, and Oliver is hilarious. This we knew already. But what else did we learn from this interview, and what does it tell us about the Snowden affair in general?

Edward Snowden’s Handlers Are Losing Their Touch

One observation right off the bat is that both the Russians and Snowden’s other advisers are losing their touch. The people around Snowden have played an expert game for the past two years, especially given the limited material (that is, Snowden himself) they’ve had to work with. They’ve done some good staging, exploited the cooperation of credulous journalists, and avoided hard questions. It is a testimony both to the fecklessness of the media and the competence of the Snowden team that Oliver was the first time Ed’s done anything even close to a real interview.

It is a testimony both to the fecklessness of the media and the competence of the Snowden team that Oliver was the first time Ed’s done anything even close to a real interview.

Why did the Russians even allow this? Seriously, did Snowden’s handlers think that Oliver, who exudes the perfect combination of mock cowardice and blustery fearlessness that is the mark of a professional smart-ass, wouldn’t open the window and point out that the meeting place was across the street from the headquarters of the Russian intelligence service? Do they not get HBO in Russia? Didn’t anyone do some homework here?

Snowden himself came prepared, at least initially. (I would love to see the full, unedited version of this one, which I assume is both wildly funny and wincingly uncomfortable.) Right at the start, however, Oliver wasn’t having any of Snowden’s pretentious and practiced responses, and when Oliver decided to have some fun, that’s when we learned more about three important things: the role of Snowden’s ego, the recklessness of Snowden’s actions, and the actual limits on programs Snowden has claimed are nearly omnipotent.

I’m A Hero, I Really Am!

Like all defectors, Snowden’s ego is heavily invested in his own heroism. Consider the look on Snowden’s face when Oliver deflated Ed’s bloated claims about how his betrayal wasn’t for his own glory, but instead to allow benighted Americans to decide these issues for ourselves. Oliver showed Snowden one clip after another of people in Times Square who had literally zero awareness of the Snowden debacle or of Snowden himself. He then said: “On the plus side, you might be able to go home, because it seems like no one knows who the f*** you are or what the f*** you did.”

Consider the look on Snowden’s face when Oliver deflated Ed’s bloated claims about how his betrayal wasn’t for his own glory.

Snowden was visibly distressed. (As Wired wrote the next morning: “Snowden’s face as he watches registers amusement, surprise, and then frank horror.”) This was not what Ed expected, and whether it was something Snowden knew already or only suspected, he didn’t like having it shoved in his face.

Of course, the right answer at that point, if Snowden were a man polished by repeated interviews and confident in his own actions, would be to smile and say: “John, that’s disturbing, and I’m glad you’re here so we can talk and get the message out more clearly.” Instead, the insecure little boy in Snowden took over: looking away, mumbling, and groping for words. (Here’s a helpful tip, Ed: both gamblers and intelligence analysts know that constantly looking down and away while speaking in a conversation is a “tell.” You should stop doing it.)

If this had been Snowden’s first week in Moscow, these might have been more understandable reactions. But he’s been doing these dog and pony shows from Russia for nearly two years. Has he really been inside a bubble so thick that no one has told him he’s over in America?

It’s Not Clear Edward Snowden Has Thought This Through

Oliver, for his part, was just getting started. For the first time, a journalist actually confronted Snowden with the recklessness of his own actions. Others have asked similar questions, and meekly accepted Snowden’s platitudes (or as we could also call them, “lies”) about how he protected the information he stole. Oliver instead did the unthinkable and asked Snowden a direct yes-or-no question: did you read all the documents you handed to others?

Without a trace of irony about his current situation, Snowden added that one is only truly secure in a prison.

Snowden’s weaselly answer—“I do understand what I turned over”—didn’t fly with Oliver. He cornered Snowden on camera like the captain of a good college debate squad tearing apart the hapless nerd who’d been asked to sub for some guy on the other team. “There’s a difference between understanding what’s in the documents and reading what’s in the documents,” Oliver said. He then added, with deadpan sarcasm: “Because when you’re handing over thousands of NSA documents the last thing you’d want to do is read them.”

Oliver then pointed out that Snowden’s revelations, fumbled by the New York Times, had done actual damage to U.S. overseas operations. Snowden’s answer? “In journalism we have to accept that some mistakes will be made.” In other words, freedom means risk; you have to break a few eggs to make an omelet. Without a trace of irony about his current situation, Snowden added that one is only truly secure in a prison.

But wait. Isn’t that exactly the same answer that proponents of national surveillance programs give? That freedom isn’t perfect, that human beings are fallible? Why is that answer good enough for Snowden’s friends at the New York Times, who’ve done demonstrable harm, but not for the National Security Agency, where the accusations of harm from Snowden and his enablers are—even by Snowden’s own admission to Oliver—entirely notional?

Hypothetical Versus Real Surveillance Threats

Oliver didn’t pursue this. He does have a comedy show to do, after all, so he instead encouraged Snowden to understand that Americans do not care about foreign surveillance, but rather care only about the security of images of their own genitalia. Snowden eventually got into the spirit of the thing, but he was uncomfortable. Grandiose heroes, after all, do not talk about pictures of men’s penises, especially when Oliver has just shoved a picture of his own penis into their hands.

Snowden’s entire case rests on what could happen if someone with evil intent were to try to seize control of a massive bureaucracy and bend it to the goal of finding out whether a random guy in New York sent his girlfriend a picture of Mr. Happy.

When Snowden finally got back to his comfort zone, however, his explanations of how the government might get pictures of your “junk” (to use Ed’s term) actually defeated his own point. Snowden—accurately, for the most part—explained how pictures of one’s, er, John Thomas transiting the global information highways could theoretically get caught up in metadata collection. Having delivered several gut punches already, Oliver this time gamely played along, noting that Americans would be horrified if they knew this was happening.

Except, of course, there is no evidence (as Snowden admits) that this is actually happening. Snowden’s explanation showed how far the government would have to go, and how much data it would have to sift, to find such pictures, read texts, and match phone calls. His entire case rests, as it has always rested, on what could happen if someone with evil intent were to try to seize control of a massive bureaucracy and bend it to the goal of finding out whether a random guy in New York sent his girlfriend a picture of Mr. Happy. (Which, as a random guy in New York admitted to Oliver on camera, he did.) In trying to generate more outrage, Snowden inadvertently made the case for calming down.

Edward Snowden Is a Lost Boy

In the end, what we saw from Moscow was the real Snowden: full of self-regard, fueled by delusions of his own importance, and unwilling—as perpetual adolescents always are—to accept responsibility for the damage his reckless actions caused. Oliver didn’t press Snowden as hard as he could have, to be sure. But when it comes to interviews with defectors, we have to take what we can get.

If Snowden can’t handle Oliver, you can be quite sure he couldn’t handle his Russian security service interrogators.

Still, even this brief look at Snowden under even the tiniest bit of journalistic pressure should end any pretenses about the inflated claims of a silly young man who once claimed he was torture-proof. Snowden is a lost boy, in over his head in a dangerous place after doing something he himself didn’t quite understand. If Snowden can’t handle Oliver, you can be quite sure he couldn’t handle his Russian security service interrogators.

In the end, the Oliver interview is so far the most important addition to what we might call The Snowden Archive. Until now, Snowden’s image has been mediated through mostly useless things like puff pieces from Barton Gellman, cheerleading by Glenn Greenwald, and a make-believe interview with Brian Williams. He has been able to say what he wants to say without fear of contradiction. Oliver may not have intended to pants Snowden in front of millions of people, but sometimes, the Cool Kids can’t help themselves. Good for Oliver, and good for us, now that we’ve had our first glimpse of the real Edward Snowden.

Tom Nichols is a professor of national security affairs at the U.S. Naval War College and an adjunct professor in the Harvard Extension School. Views expressed here are his own. Follow him on Twitter, @RadioFreeTom.